Ethyl chloroformate → 2-bromo-4,6-difluoro-N-carbethoxy aniline

HRID 1272232

반응식

HRID 1272232 반응식
[Br:1][C:2]1[CH:8]=[C:7]([F:9])[CH:6]=[C:5]([F:10])[C:3]=1[NH2:4].Cl[C:12]([O:14][CH2:15][CH3:16])=[O:13].C(OCC)(=O)C.CCCCCC>N1C=CC=CC=1>[Br:1][C:2]1[CH:8]=[C:7]([F:9])[CH:6]=[C:5]([F:10])[C:3]=1[NH:4][C:12]([O:14][CH2:15][CH3:16])=[O:13]

참가 물질

5

반응물 3

HCID 10928Ethyl chloroformateHCID 1362852-Bromo-4,6-DifluoroanilineHCID 21226206Ethyl acetate hexane

생성물 1

HCID 170685752-bromo-4,6-difluoro-N-carbethoxy aniline수율 94%

시약·촉매·용매 1

HCID 1049Pyridine용매

실험 절차

To a vigorously stirred solution of 2-bromo-4,6-difluoro aniline (100 g, 0.48 mol) in pyridine (400 mL), at 0° C., is added ethyl chloroformate (70 ml, 0.73 mol) at a rate to keep the temperature below 5° C. When addition is complete, the mixture is stirred at 0° C.–5° C. an additional 2 hours while monitoring by TLC (20% ethyl acetate/hexane, UV). The reaction is then allowed to warm to room temperature, filtered and the filtrate concentrated. The residue is dissolved in diethyl ether/ethyl acetate (500 ml/250 ml) and washed with H2O, 2.5 N HCl, aqueous NaHCO3, brine, dried (Na2SO4), filtered, concentrated, and triturated with petroleum ether to give 126 g of 2-bromo-4,6-difluoro-N-carbethoxy aniline (94%).

후처리

  1. customthe temperature below 5° C
  2. additionWhen addition
  3. filtrationfiltered
  4. concentrationthe filtrate concentrated
  5. dissolutionThe residue is dissolved in diethyl ether/ethyl acetate (500 ml/250 ml)
  6. washwashed with H2O, 2.5 N HCl, aqueous NaHCO3, brine
  7. dry with materialdried (Na2SO4)
  8. filtrationfiltered
  9. concentrationconcentrated
  10. customtriturated with petroleum ether

출처 및 근거

ORD 기록
ord-37e6d963345f4c2dbbe69c4338ef4c19
출처 데이터셋
uspto-grants-2007_04
특허 번호
US07208505B2

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